Arylazoaroylguanylureas and their salts



Patented Jan. 9, 1945 UNITED atom-is ABYLAZOAROYLGUANYLUREAS AND THEIR SALTS Jack '1. Thurston, Riverside, Conn, aslignor to American Cyanamld Company, New York N. Y., a corporation of Maine No Drawinl.

Application May 28, 1943, Serial No. 488,891

" 9 Claims. (01. 200-163) This invention relates to new azo dyestuffs and to their preparation. More particularly, the new azo dyes to be described and claimed herein may be broadly designated as arylazoaroylguanylureas.

The arylazoaroylguanylureas of the present invention may be represented by the general formula 11 NH H 0 ArN=N-Ac- -l l'- ll NHi in which Ar and Ac are aromatic radicals. Ar and- Ac may be the same, or diflerent, typ of arcmatic radical and may-have various types and kinds of substituent groups as will be shown hereinafter.

Azo dyes having the above general formula may be prepared by diazotizing an aromatic acyl guanylurea which contains an airline group in the aromatic ring and then coupling it with an aromatic coupling component, containing an amino or .hydroxyl group attached to the aromatic ring, through the diazoic group. Amon th aromatic acyl guanylureas which may be diazotized and coupled with aromatic components to form new dyes are those such as p-aminobenzoylguanylurea, m-aminobenzoylguanylurea, 3-amino-5-hydroiiybenzoylguanylurea, -4-amino-u-naphthoylguanylurea, 5 amino p naphthoylguanylurea,

aminophenylacetylguanylurea, aminophenylstearoylguanylurea, p-(4 aminophenyl) propionylguanylurea, m-amino-cinnamylguanylurea, 4- (4' amino-2 -nitrophenyl) --butene-3-oyl-guanylurea, 4-aminophthaloyl-bis-guanylurea, 2 (4-aminobenzoyl) benzoylguanylurea, 3 aminophenoxyacetylguanylurea, 3 aminophenoxydiethoxyacetylguanylurea and the like.

These aromatic acyl guanylureas are prepared by hydrolyzing the terminal --CEN group of a whether carbocyclic or heterocyclic, having conjugated doublebonds. Familiar compounds of this 'class are those belonging to the benzene, naphthalene, .pyrazolone, carbazole, benzothiazole, 1,2,4-triazole, 3-hydroxyindole andother series. These compounds may be substituted with alkyl, aryl, cycloalkyl, halide, hydroxy, nitro, cy-

ano, sulio, sulfamido, carboxy, carbonyl, carbamyl, amino and other radicals as will appear from the specific compounds named below and from the specific illustrative examples.

Specific instances of suitable coupling compounds of these types are: the hydroxy benzenes and substituted hydroxy benzenes such as 1,3-dihydroxy benzene, 2,6 dihydroxybenzoic acid, 1,2,3-trihydroxy benzene, guaiacol, m-nitrophenol, chlorophenols, naphthols, aminonaphthols, naphthol sulfonic acids, 'phenolsulfonic acids,

eta; the amino benzenes and substituted amino benzenes such as aniline, metanilic acid, dimethylaniline, diethylaniline-m-sulfonic acid, ethylbenzylaniline, ethylbenzylaniline sulionic acid, 1,3-diaminobenzene, orthoand meta-toluidine, p-xylidine, 2,5-dihydroxyalkylaminobenzene, mtoluylene-diamine, phenylazoaniline, 3 aminophenol-G-sulfonic acid, o-methoxyaniline, p-ethoxyaniline, ortho-aminobenzoic acid, etc.; the hydroxyand amino naphthalenes such as aand pnaphthols, aand fi-naphthylamines, the naphthylamine sulfonic acids, l-naphthol-3-sulfonic acid. 1-amino-8-nitro-2-naphthol-4-sulionic acid, 1,8-dihydroxynaphthalene-3,6-disulfonic acid, 1- chloro-8-naphthol-3,6-disulfonic acid, 2-naphthol-7-sulfonic acid, 2-amino.-8-naphthol-6-sulionic acid, 2-naphthol-6,8-disulfonic acid, 2-acetylamino-5-naphthol-7-sulfonic acid, 2-N-p-hydroxyethylamino-8-naphthol-6-sulfonic acid, 1,8- amidonaphthol-3,6-disulfonic acid, 7-hydroxy-lnaphthyl-m-hydroxyphenylamine, etc.; the arylides of naphthoic acids as for example the benzidide oi B-hydroxynaphthoic acid, 2-hydroxy-- naphthanilide, B-hydroxynaphthoic anilide, etc.; pyrazolones and pyrazyl pyrazolones such as 3- methyl-5-pyrazolone, l phenyl 3 methyl 5 pyrazolone, 1 (4'-sulfophenyl) -3-methyl-5-pyrazolone, 1 (2' naphthyl) -3-methyl-5- pyrazol0ne-8'-su1fonic acid, and the like; ortho-' and meta-hydroxybenzoyl guanylurea, o hydroxyphenoxyacetylguanylurea, aminohydroxybenzoylguanylurea, orthoand meta-hydroxybenzoyldicyandiamide, o hydroxyphenoxyacetyldicyandiamide, aminohydroxybenzoyldicyandiamide, 'etc.; arylides of acetoacetic acid such as diacetoacetictolidide, furoylacetic acid, hydroxy-dibenzothiophene carboxylic acids, etc.; and those condensation products of aryl amines with a-hydroxymethane sulfonic acids such as specifically N-omethylphenylaminomethanesulfonic acid, etc.

By selecting appropriate coupling components it is possible to prepare dyes having particular utility in dyeing fabrics of cellulosic fibers such as cotton, regenerated cellulose, cellulose esters and ethers, etc.; wool, silk, nylon and other natural andsynthetic fibers. Dyes maybe formed which are either acidic or basic in character.

They may be formed having solubilizing groups, such as sulfonic or carboxyl groups, or not, as desired. Some of the dyes may be metallized with copper, chromium, iron, manganese, cobalt, nickel, etc., and made more stable. For example, when the radicals Ar and Ac each have hydroxyl groups, hydroxyl and carbonyl, hydroxyl and amino, or hydroxyl and carboxyl groups in ortho position to the azo bridge the dyes may be metallized. A typical metallizable dye of this type can be made by diazotizing p-amino-m-hydroxybenzoylguanylurea, and coupling it with p-naphtholsulionic acid in alkaline solution. The dyes of the present invention may also be employed in.

the preparation 01' printing inks, textile printing pastes, colored lacquers, colored plastic compositions, for dyeing paper and in other related fields Most of the new dyestufl's covered by the general formula H NE E o annals-Lat.

may also be prepared by coupling an amino or hydroxy aromatic acyl guanylurea to a diazotized aryl amine. Typical amines which can be diazotized and reacted with aromatic-acyl guanylureas having activating groups thereon are the following: aniline and substituted anilines such as toluidine, 2,4-dimethylaniline, monofluoroaniline, monochloroanilines, 2,5 dichloroaniline, m aminobenzotrifluoride, 2-methyl-3-ch1oroaniline, 2-methyl-4-chloroaniline, 2-methyl-5-chloroaniline, 2-methyl 4 chloro 5 bromoaniline, 4-

' methyl-2,5-dichloroaniline, 2-methyl-4-nitroaniline, 2-nitro-4-chloroaniline, etc.; ether derivatives of primary aromatic amines such as o-anisidine, 2-methoxy-5-methylaniline, 2,5-dimethox'yaniline, Z-methoxyl-naphthylamine, 2-amlnodiphenylether, 2 methoxy 5 chloroaniline, 3-

bromo-G-ethoxyaniline, 4-amino-4'-chloro di phenylether, 2-methoxy-4-nitroaniline, 2-methoxy- B-nitroaniline, 2-methoxy-4-nitro-5-methylaniline; monoacyl derivatives oi aromatic diamines, such as N-hexahydrobenzoyl-p-phenylenediamine, N hexahydrobenzoyl p-toluylenediamine, N-ben'zoyl-p-phenylenediamine; monoacyl derivatives of diamino-phenol ethers, such as 2-benzoylamino-4-amino-anisole, z-hexahydrobenzoylamino-S-amino-anisole, 2 amino-5- phenoxyacetylamino-hydroquinone diethylether,

methyl-i-amino-azobenzene, and the like.

In addition to the above there are numerous ass-1,07:

falling within the scope of the present invention. An amine of ,this type is 2,6-chloro-l,4-phenylenediamine.

Diamines in which both amino groups are dl-. azotized to form tetrazo compounds will also condense with amino and hydroxy aromatic acyl guanylureas. Amines of thi class are benzidine. p-phenylenediamine, c-toiidine, 2,6-diethoxy-L4- phenylenediamine, o-dianlsidine, 4,4'-diaminostilbene, 4,4 diaminodiphenylamine, 1,5 di aminonaphthalene and the like.

Diazo and tetrazo compounds derived from aromatic amines of the heterocyclic type can also be reacted with amino and hydroxy aromatic acyl guanylureas. Typical of these heterocyclic amines are Z-amino-carbazole, 3,6-diamino-carbazole, 1-amino-5-tluorobenzothiazole, 2-amino-' 3-nitrodibenzothiophene, 3-aminobenzol,2,4-triazole and 8 amino (4'-aminobenzo) -1,2,i-triazole.

The coupling of diazotized amines or diazotized aromatic acyl guanylureas with coupling components of the class described herein is normally carried out in slightly alkaline medium at low temperatures as in conventional diazoic coupling procedures. In certain cases, however, the coupling is preferably effected in a slightly acid medium. The reaction does not require a critical proportion of reagents butordinarily the two components are used in substantially equi-molecular proportions. In the preparation of certain tetrazo dyes, however, two molecular proportions of aromatic acyl guanylurea are used for each molecular proportion of the tetrazonium. reactant.

Most of these arylazoaroylguanylurea dyes may also be prepared from the corresponding arylazoaroyldicyandiamides by hydrolysi of the terminal -CEN group of the arylazoaroyldicyandiamide with an acid having a dissociation constant of at least 1x10 The arylazoaroyldicyandiamides, which are also new compounds, are described and claimed in my co-pending application Serial No. 477,275 filed Feb. 26, 1943. These compoundsare converted into compounds covered by the present invention by hydrolysis with acids such as hydrochloric, sulfuric, sulfurous, phosphoric, phthalic, chloracetic, toluenesultonic, sultamic and others, as described in the aforementioned application of Kaiser and Thurston, Serial No. 463,666. Since the preparation of acylated guanylureas from acylated dicyandiamides is broadly claimed in this latter aparomatic diamines in which only one of the droxy aromatic acyl guanyiureas to mm dyes plication this method of prepar ng arylazoaroylguanylureas is not specifically claimed in this application.

As' previously indicated, dyes may be formed having many different characteristics and generalizations as to the outstanding properties of these products are difllcult to'make. Their solubility characteristics vary considerably, some being water soluble and some water insoluble. Most of them are difllcultly soluble in both acids and alkalis in the absence of solubilizing groups. In general they are soluble in organic solvents such as pyridine, dioxane, the monomethyl and monoethyl ether of ethylene glycol, etc.

The preparation of a typical aromatic acyl guanylurea and the preparation or representative dyestufls from aromatic acyi guanylureas will now be illustrated in the following specific examples. Example are also given of the preparation of arylazoaroylguanylureas from corresponding arylazoaroyldicyandiamides. It should be understood, of course, that the invention is not limited to the particular dyestufls described herein or the particular details or the processes set forth. All parts are by weight unless otherwise indicated.

Example 1 185 parts of p-nitrobenzoyl chloride was dissolved in 896 parts of acetone and added to a cold mixture of 306 parts of 50% sodium hydroxide, 100 parts of dicyandiamide, 396 parts of acetone and 200 parts of water. The temperature was kept at 25-10" C. and the addition was complete in a half-hour. The mixture was then diluted with water, neutralized and filtered. The material was then purified by dissolving in an excess of potassium hydroxide solution and cooling, whereupon the potassium salt of p-nitrobenzoyldicyandiamide was precipitated. The acyl dicyandiamide was recovered from its salt by dissolving in water and neutralizing with hydrochloric acid.

a 955 parts of FezSO4.7H2O was dissolved in 1500 parts of water and the solution heated to refluxing temperature with stirring. In the meantime 1250 parts of water was heated almost to boiling, 90 parts of concentrated ammonium hydroxide with stirring of 32.8 parts of sodium acetate. A bright orange dye formed immediately. The

product had the folowing structural formula.

OHNHHO The dye was soluble in dilute acids with a color mixture.

change to a. bright pink-red.

Example 2 ner. The excess nitrous acid was then destroyed with sodium sulfamate.

9.5 parts of dimethyl aniline and 32.8 parts of sodium acetate were then added to the reaction Addition of the latter reagent caused the formation of a deep red dye having the followin ormula:

OHNHH II I II I O II was added and then 100 parts of p-nitro-benzoyldicyandiamide was added. This latter solution was added to the boiling ferrous sulfate solution followed by sufllcient ammonium hydroxide (about 450 parts) to make the mixture faintly alkaline. Boilin was continued for 10 minutes and the mixture was then cooled in an ice bath. The solution was filtered to remove insoluble material which was extracted with dilute alkali to remove the p-aminobenzoyldicyandiamide contained therein. Upon neutralization This product was soluble Example 3 25 parts of p-aminobenzoyldicyandiamide was dissolved in a solution of 54 parts of 10% sodium hydroxide and 100 parts of water and poured slowly into a water-acid solution containof the alkaline solution p-aminobenzoyldicyandiamide was obtained as a pale yellow material decomposing when heated'at 235-237" C.

20 parts by weight of p-aminobenzoyldicyandiamide obtained by reduction of p-nitrobenzoyldicyandiamide with ferrous sulfate as described above was treated with 200 parts by weight of 2% hydrochloric acid at room temperature for one hour. The insoluble matter was filtered and the solution neutralized with dilute ammonia to a pH of about 5.0. The precipitate of the p-aminobenzoylguanylurea-was boiled for a short time with a slight excess of 10% hydrochloric acid to insure complete conversion of the p-aminobenzoyldicyandiamide to p-aminobenzoylguanylurea. The latter product was recovered by filtering the precipitate obtained upon neutralizing the solution with ammonium hydroxide as before. The p-aminobenzoylguanylurea thus obtained had a faintly yellow color and decomposed when heated at 170-175 C. Upon recrystallization from a methanol-water mixture a. colorless product was obtained which decomposed at 178-180 C.

22.1 parts by weight of p-aminobenzoylguanylurea was dissolved in 150 parts by weight of 10% hydrochloric acid. A solution of 6.9 parts of sodium nitrite in 50 parts of water was added slowly to the above at 3 to 5 C. until the theoretical amount of sodium nitrite had been added. After stirring for about 15 minutes sufiicient sodium sulfamate was added so that a sample of the reaction mixture gave only a faintly positive reaction to the starch-potassium iodide test.

9.3 parts by weight of aniline was then added to the reaction mixture followed by the addition ing 235 parts of 10% hydrochloric acid and 900 parts of water with stirring at 5 C. A solution of 17 parts of sodium nitrite in parts of water was aded slowly to the above until the theoretical amount of sodium nitrite had been added, 1. e. about 60 parts of the sodium nitrite solution. After 20 minutes a small amount of dilute sodium sulfamate solution was added until samples of the reaction mixture were negative to the starch-potassium iodide test;

The neutralized solution was then poured into i a solution containing 19.4 parts of ,B-naphthol, 54 parts of 10% sodium hydroxide and 41.2 parts of sodium carbonate in 1000 parts of water. After 4 to 5 hours of stirring, the red dye which had precipitated out was filtered, washed and vacuum dried. 10 parts by weight of the dried product was treated with an equal weight of concentrated hydrochloric acid at room temperature for about 10 minutes. The reaction mixture was then diluted with water and filtered. The product was believed to have the following structure:

An aqueous suspension of the dye had a dull red color and was only slightly soluble in dilute hydrochloric acid.

Example 4 20.3 parts of crude m-aminobenzoyldicyandiamide was d ssolved in a solution of 88.8 parts of 10% sodium hydroxide and 100 parts of water and poured slowly into a water-acid solution containing 158 parts of 10% hydrochloric acid and 100 parts of water with stirring at C. A boiled with 25 parts of 5% hydrochloric acid for solution of 6.9 parts of sodium nitrite in 50 parts 5 minutes whereupon a light yellow-orange dye of water was added slowly to the above until the was precipitated. The product having the folstarchpotassiumiodide test was faintly positive; lowing structural formula This required the addition of about 75% of the 6 nitrite solution 0 i NH I 0 The neutralized solution was then poured into CH' N=NOE a solution of 24 parts of 1-amino-8-hydroxy- 3,6-disulfonaphthalene, 49 parts of sodium hydroxide and 4.1 parts of sodium acetate in 4 750 parts of water. A scarlet-red dye believed to b was recovered by filtration, washed and dried.

This arylazoaroylguahylurea dye was very slight- HIN 011' 1y soluble in dilute hydrochloric acid but dis- 1 E f E3 soved in dilute caustic soda with a red color.

N=N- N-' -N-CN 6 110,8 25 parts ofp-aminobenzoyldicyandiamide was diazotized' as described in Example 6 and added precipitated immediately. Arter- 4 to 5 hours of to 1500 pa of a ut ainin 15.5 parts stirring the dye was filtered, washed and vacu- 0 i az nic acid and 88 parts of a 10% Sodium um d d, hydroxide solution. Sufficient sodium acetate 10 parts of the dry dye was dissolved in about Was added to bring the D 0 -5- te Standparts of cold 50% sulfuric acid. After standms r 3 hours in n e bat t e e owown ing for 10 to 15 minutes the solution was diluted 25 dye which had formed as fi tered and washed. with water to give a precipitate lighter in color Treatment Of the yellow-brown ye with hot 5% than the original dye. The precipitate was rehydrochloric acid immediately converted it to an covered, washed and dried. It was believed to live-yellow dye havin the followin formula: havethe following structural formula: coon so 0 H H H 0 CC with... .55 irr This dye was slightly s'oluble'in acid but soluble This arylazoaroylguanylurea dye was insoluble in alkali with p brown 0 0 ln hot dilute hydrochloric acid but was soluble in solutions of caustic soda. Example 7 A somewhat similar dye may also be prepared 40 16.2,parts of 2,5-dichloroaniline was dissolved by using two molar quantities of the diazotized on heating in 236 parts of 10% hydrochloric m-aminobenzoyldicyandiamine for each molar acid. The solution was then cooled to 5 C. quantity of the 1-amino-8-hydroxy-3,6-disulfoand 7.5 parts of solid sodium nitrite added to obnaphthalene followed by hydrolysis with sulfuric tain a clear solution. After 15- minutes a trace acid. In thiscase the product is believed to have of gum was removed by filtration.

the following formula: 22.4 parts of m-hydroxyphenoxyacetyldi- Hm 0H 0 1 1 NH 1 1 o o Iii NH I! 0 sou-(LN- --N-h N=N N=N N --N-g-NH= Q HOIS SOlH Example 5i: cyandiamide was suspended in a solution of 88 parts of 10% sodium hydroxide and 40 parts of sodium carbonate in 1000 parts of water. To this suspension was added-the filtered diazonium solution prepared above. The brown dye which formed immediately was filtered, washed and dried. A quantity of this material was macerated with an equal quantity of concentrated hydrochloric acid at room temperature for a few 25 parts of p-amlnobenzoyldicyandiamide was dissolved in a solution of 88.8 parts of 10% sodium hydroxide and 100 parts of water and poured slowly with stirring into a water-acid solution. containing 204 parts of 10% hydrochloric acid and 100 parts of water cooled to 00 5 C. A solution of 6.9 parts of sodium nitrite in 100 parts of water was added slowly to the above until the starch-potassium iodide test was minutes Upon dflution of the reaction mixture with water a guanylurea dye of a light brown i g i' g 52 2;; fifig z gigfig 2 of color was obtained as an insoluble residue. The

HA parts of 1 pheny1 3 methy1 5 pymz1one dye was believed to have the following formula:

was suspended in a solution of 88 parts of 10% 01 sodium hydroxide in 1000 parts of water. The Q-N=N o H NE E o diazotized p-aminobenzoyldicyandiamide was (/1 ,t 1

poured slowly into the suspension, the pH was 0 adjusted to 7.5 to 8.0 and the reaction mixture stirred 2 to 3 hours in an ice bath. The mixture was neutralized and the orange dye filtered, washed and dried. Example 8 10 parts of the dry product thus obtained was. 15.8 parts of m-nitroanlline was S p d in 236 arts of 10% hydrochloric acid. The suspension was cooled to 5 C. and 7.5 parts of solid sodium nitrite was added in 1 to 2 minutes. A clear solution resulted.

22.4 parts of m-MdroXYphenoxyaqetyldicyandiamide was suspended in a solution of 44 parts of 10% sodium hydroxide and 70 parts of sodium carbonate in 1000 parts of water. To this suspension was added the diazonium solution obtained above. An orange red dye formed immediately- This dye was recovered by filtration and dried. 15 parts of the dry product was treated with an equal weight'of concentrated hydrochloric acid at room temperature for a few minutes. The re-' action mixture was then, diluted with water whereupon a semi-colloidal light red suspension of the dye was obtained. The dye was flocculated by the addition of sodium chloride. following structural formula:

N=N I Q NHK 0 a lg Example 9 11 parts by weight of m-aminobenzoylguanyiurea was dissolved in a. solution of 114 parts by weight of 10% hydrochloric acid and 100 parts by weight of water. The solution was then cooled 'dye precipitated immediately. After stirring the mixture in an ice bath for 3 hours the dye was filtered, washed and air-dried. It was believed to have the following structural formula:

OHNHHO The orange dye was soluble in dilute hydrochloric acid with an orange red color.

Example 10 7.2 parts by weight of p naphthol was dissolved in 20 parts by weight of a warm 10% solution of sodium hydroxide and the solution cooled in an ice bath. To this cold solution a diazotized m -aminobenzoylguanylurea solution prepared exactly as described in the first paragraph of Example 9 was added in one portion. A bright red dye formed at once. After stirring first in an ice bath for one-half hour and then at room temperature for 2 to 3 hours the dye was filtered and washed. It was believed to have the following structure:

It had the The dye was faintly soluble in hydrochloric acid but was more easily soluble in dilute solutions of This dye was insoluble in acid and soluble in caustic soda with development of a deep red color.

Example 11 13.1 parts by weight of p naphthanilide was dissolved in a little methanol and added to a cold solution of diazotized m-aminobenzoylguanylurea prepared as described in the first paragraph of Example 9. A red dye formed at once. After stirring for two hours at room temperature, the dye was filtered and washed with water. It was believed to have the following formula:

o I NC4H| The dye was insoluble in dilute hydrochloric acid and was partly soluble in alkali to give a red colored solution.

Example 12 11.8 parts by weight of gamma acid was dissolved in 20 parts by weight of a 10% solution of sodium hydroxide and then cooled in an ice bath. A; solution of diazotized aminobenzoylguanylurea, as in Example 9, was quickly added to the gamma solution. A deep reddish brown dye formed at once which was believed to have the structural formula:

o 1 NH 1 1 0 -N- -N- -NH,

alkaline solution with deepening of the color.

' Example 13 9.4 parts of fl-oxynaphthoic acid was dissolved in water containing 2 parts of sodium hydroxide and the cold solution was combined with a diazotized solution of m-aminobenzoylguanylurea. A bright scarlet dye was precipitated. After stirring for 1 hour, the dye was recovered by filtration. It had the following structural formula:

OHNHHO This dye was insoluble in acid but soluble in alkali to give a deep red colored solution.

What I claim is: 1. Azo dyestuffs of the general formula:

in which Ar is an aromatic. radical, and Ac is an aromatic radical of the group consisting of radicals of the benzene andnaphthalene series. 2. A20 dyestuffs of the general formula:

H NH H o in which Ar is an aromatic radical and Ac is an aromatic radical of the benzene series.

3. A20 dyestuffs of the general formula:

0 El r m I 0 Ar-N=N-Ao Nb-N .-NH:

in which Ar is an aromatic radical and Ac is a' phenyl radical.

4. A20 dyestufls oi the general formula:

in which Ar and Ac are aromatic radicalsof the benzene series. A

5. A20 dyestufls of the general formula:

0 1 NH 1 0 ArN=NAc( J-N N- -NH: I in which Ar is an aromatic radical of the naphthalene series and Ac is an aromatic radical of the benzene series.

' 6. An azo dye having the formula:

in which Ar is an aromatic radical of the pyrazolone series and Ac is an aromatic radical of the benzene series.

8. A method of preparing dyestuffs of the general formula:

' radical of the group consisting of radicals oi the benzene and naphthalene series.

9; A method of preparing dyestufls oi the seneral'iormula:

HNHHO in which Ar is an aromatic radical and Ac is an aromatic radical of the group consisting of radicals of the benzene and naphthalene series which comprises the steps of diazotizing an aromatic amine and coupling it to an aromatic acylguanylurea of which the aromatic radical is a radical of the group consisting of radicals of the benzene and naphthalene series. I

- JACK T. 'I'HURSTON. 

